Thionyl Chloride → 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonyl chloride

HRID 544679Notes

Reaction equation

HRID 544679 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([C:16]([OH:18])=O)=[CH:3][CH:2]=1.S(Cl)([Cl:21])=O>>[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([C:16]([Cl:21])=[O:18])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 132813416,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid

Product 1

HCID 132813426,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonyl chloride

Procedure

Under a dry nitrogen atmosphere a stirred solution of 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid (3.4 grams, 0.0142 mole) in thionyl chloride (10 ml) was heated at reflux for 1.5 hours. The excess thionyl chloride was removed by distillation under reduced pressure. Benzene (10 ml) was added and then removed by distillation under reduced pressure to leave 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonyl chloride as a residue.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe excess thionyl chloride was removed by distillation under reduced pressure
  3. additionBenzene (10 ml) was added
  4. customremoved by distillation under reduced pressure

Sources & evidence

ORD record
ord-ea6642ff6b9a431aa9fa5e8667577564
Source dataset
uspto-grants-1984_05
Patent number
US04451484

Reaction notes

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